CHCH CH-CH₂ H-CI CH₂ CH CH CH₂ + CI I CH₂CH=CH-CH₂ CI II At 0°C, the following product composition is observed: product I (71%), product II (29%). At 42°C, the following product composition is observed: product I (15%), product II (85%). ANSWER THE FOLLOWING QUESTION: Why does the addition product I predominate at the lower temperature (0°C)? At lower temperature, the reaction is kinetically controlled: product I forms faster, so product I predominates. O Product I predominates at lower temperature because it has more i electron delocalization than product II. Product I is less sterically hindered, so it predominates. At lower temperature, the reaction is equilibrium controlled: product I is more stable than product II, so product I predominates. ↑

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter10: Organohalides
Section10.SE: Something Extra
Problem 45AP
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The reaction of 1,3-butadiene with HCl produces two addition products. (See below) The relative amounts of the products that form is strongly temperature dependent. Here are the results: At 0oC, the following product composition is observed: product I (71%), product II (29%). At 42oC, the following product composition is observed: product I (15%), product II (85%). ANSWER THE FOLLOWING QUESTION: Why does the addition product I predominate at the lower temperature (0oC)?
The reaction of 1,3-butadiene with HCI
produces two addition products. (See below)
The relative amounts of the products that form
is strongly temperature dependent. Here are
the results:
CH CH CH CH₂
H-CI
CHỊCHÍCH CH3 +
I
CI
CH₂ CH CH-CH₂
CI
II
At 0°C, the following product composition is
observed: product I (71%), product II (29%).
At 42°C, the following product composition is
observed: product I (15%), product II (85%).
ANSWER THE FOLLOWING QUESTION: Why
does the addition product I predominate at the
lower temperature (0°C)?
At lower temperature, the reaction is
kinetically controlled: product I forms
faster, so product I predominates.
Product I predominates at lower
temperature because it has more
electron delocalization than product II.
Transcribed Image Text:The reaction of 1,3-butadiene with HCI produces two addition products. (See below) The relative amounts of the products that form is strongly temperature dependent. Here are the results: CH CH CH CH₂ H-CI CHỊCHÍCH CH3 + I CI CH₂ CH CH-CH₂ CI II At 0°C, the following product composition is observed: product I (71%), product II (29%). At 42°C, the following product composition is observed: product I (15%), product II (85%). ANSWER THE FOLLOWING QUESTION: Why does the addition product I predominate at the lower temperature (0°C)? At lower temperature, the reaction is kinetically controlled: product I forms faster, so product I predominates. Product I predominates at lower temperature because it has more electron delocalization than product II.
CH=CH-CH-CH₂
H-CI
CH₂ CH CH CH₂ +
CI
I
CH, CHCHCH,
CI
II
At 0°C, the following product composition is
observed: product I (71%), product II (29%).
At 42°C, the following product composition is
observed: product I (15%), product II (85%).
ANSWER THE FOLLOWING QUESTION: Why
does the addition product I predominate at the
lower temperature (0°C)?
At lower temperature, the reaction is
kinetically controlled: product I forms
faster, so product I predominates.
Product I predominates at lower
temperature because it has more
electron delocalization than product II.
Product I is less sterically hindered, so it
predominates.
At lower temperature, the reaction is
equilibrium controlled: product I is more
stable than product II, so product I
predominates.
Transcribed Image Text:CH=CH-CH-CH₂ H-CI CH₂ CH CH CH₂ + CI I CH, CHCHCH, CI II At 0°C, the following product composition is observed: product I (71%), product II (29%). At 42°C, the following product composition is observed: product I (15%), product II (85%). ANSWER THE FOLLOWING QUESTION: Why does the addition product I predominate at the lower temperature (0°C)? At lower temperature, the reaction is kinetically controlled: product I forms faster, so product I predominates. Product I predominates at lower temperature because it has more electron delocalization than product II. Product I is less sterically hindered, so it predominates. At lower temperature, the reaction is equilibrium controlled: product I is more stable than product II, so product I predominates.
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